Catalyst-Controlled Inverse-Electron-Demand Hetero-Diels−Alder Reactions in the Enantio- and Diastereoselective Synthesis of Iridoid Natural Products

2003 ◽  
Vol 5 (14) ◽  
pp. 2563-2565 ◽  
Author(s):  
David E. Chavez ◽  
Eric N. Jacobsen
Keyword(s):  
Natural Products ◽  
Diels Alder ◽  
Diastereoselective Synthesis ◽  
Inverse Electron Demand ◽  
Electron Demand

Dual C–H functionalization of N-aryl tetrahydroisoquinolines: a highly diastereoselective synthesis of dibenzo[a,f]quinolizines via visible-light induced oxidation and inverse electron-demand aza-Diels–Alder reaction

2016 ◽  
Vol 52 (6) ◽  
pp. 1190-1193 ◽  
Author(s):  
Guo-Qiang Xu ◽  
Chen-Guang Li ◽  
Ming-Qian Liu ◽  
Jian Cao ◽  
Yong-Chun Luo ◽  
...  
Keyword(s):  
Visible Light ◽  
Alder Reaction ◽  
Diels Alder ◽  
Visible Light Photocatalysis ◽  
Diastereoselective Synthesis ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

Dual C–H functionalization of amines with high diastereoselectivity is developedviavisible-light photocatalysis and inverse electron-demand aza-Diels–Alder reaction.

Stereoselective construction of a key hydroindole precursor of epidithiodiketopiperazine (ETP) natural products

2014 ◽  
Vol 50 (68) ◽  
pp. 9690-9692 ◽  
Author(s):  
Minghao Feng ◽  
Xuefeng Jiang
Keyword(s):  
Natural Products ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Electron Demand

The functionalized hexahydroindole scaffold of ETPs was constructed by an asymmetric strategy involving a diastereoselective inverse electron-demand Diels–Alder (IEDDA) reaction.

Diastereoselective Synthesis of Functionalized Tetrahydropyridazines Containing Indole Scaffolds via Inverse-Electron-Demand Aza-Diels–Alder Reaction

2021 ◽  
Author(s):  
Taotao Chen ◽  
Chao Che ◽  
Zhefei Guo ◽  
Xiu-Qin Dong ◽  
Chun-Jiang Wang
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diastereoselective Synthesis ◽  
Inverse Electron Demand ◽  
Catalyst Free ◽  
Diels Alder Reaction ◽  
Electron Demand

An unprecedented base-promoted and catalyst-free inverse-electron-demand aza-Diels-Alder (IEDDA) reaction between the easily available in situ generated azoalkenes and 3-vinylindoles has been developed. This efficient protocol afforded structurally important tetrahydropyridazines containing...

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

2019 ◽  
Author(s):  
Zijian Guo ◽  
Bruno Oliveira ◽  
Claudio D. Navo ◽  
Pedro M. S. D. Cal ◽  
Francisco Corzana ◽  
...  
Keyword(s):  
Protein Modification ◽  
Cross Reactivity ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
On Demand ◽  
Strained Alkenes ◽  
Electron Demand

<p>Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (<i>t</i><sub>1/2</sub>≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.</p>

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

2019 ◽  
Author(s):  
Zijian Guo ◽  
Bruno Oliveira ◽  
Claudio D. Navo ◽  
Pedro M. S. D. Cal ◽  
Francisco Corzana ◽  
...  
Keyword(s):  
Protein Modification ◽  
Cross Reactivity ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
On Demand ◽  
Strained Alkenes ◽  
Electron Demand

<p>Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (<i>t</i><sub>1/2</sub>≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.</p>

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